In 1984, he briefly worked as a sports anchor at WCVB-TV in Boston before heading to Los Angeles to work at KTLA and KCBS.His work there earned him 11 Golden Mike Awards In 1992 Olbermann joined ESPN's Sports Center, a position he held until 1997 with the exception of a period from 1993–94 when he was at ESPN2.Olbermann and Patrick referred to this segment as "The Big Show", just as their book was known.Patrick often introduced Olbermann with the tagline "saving the democracy", a nod to his work on Countdown.In 2007, ten years after Olbermann's departure, in an appearance on the Late Show with David Letterman, he said, "If you burn a bridge, you can possibly build a new bridge, but if there's no river any more, that's a lot of trouble." During the same interview Olbermann stated that he had recently learned that as a result of ESPN's agreeing to let him return to the airwaves on ESPN Radio, he was banned from ESPN's main (Bristol, Connecticut) campus.Olbermann later left that show to be an anchor and executive producer for The Keith Olbermann Evening News, a sportscast similar to Sports Center that aired weekly on Sunday evenings.
he later co-authored a book with Patrick called The Big Show about their experiences working at Sports Center; he also said that the short-lived ABC dramedy Sports Night was based on his time on Sports Center with Patrick, ABC having been co-owned with ESPN since 1985 (ESPN now produces all sports coverage on ABC, which is branded ESPN on ABC).Olbermann hosted a web series for titled The Closer with Keith Olbermann while covering the 2016 US presidential election and re-titled The Resistance after the victory of Donald Trump.As a teenager he often wrote about baseball card-collecting and appeared in many sports card-collecting periodicals of the mid 1970s.He is also referenced in Sports Collectors Bible, a 1979 book by Bert Sugar, which is considered one of the important early books for trading card collectors.In the early-to-mid 1980s he was a sportscaster on the old WNEW 1130-AM radio station in New York City.
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Early in 1997 Olbermann was suspended for two weeks after he made an unauthorized appearance on The Daily Show on Comedy Central with then-host and former ESPN colleague Craig Kilborn.